Chem 31 Prob Set Org Mech Nucleophilic

CHEM 31 PROBLEM SET: ORGANIC MECHANISMS - NUCLEOPHILIC NAME: _________________________________ 1. Which one of the Grignard reactions below could give rise to CH3CH2CH(OH)CH2CH3? (A) (B) (C) (D)

propanone and methyl Grignard butyl Grignard and acetaldehyde ethyl Grignard and propionaldehyde methyl ethyl ketone and methyl Grignard

2. Indicate the reagents and/or compounds required to carry out the transformation shown below: ? O 1,6-hexanedione

SEC. _______________

SCORE: ____________

5. What is the principal product of the following reaction? H+ O + 2 CH 3OH

(A) (B) (C) (D) (E)

5,5-dimethyl pentanal cyclopentanone dimethyl ketal 3-methyl-1,5-pentanedione 2-methyl cyclopentanone cyclopentane dimethyl acetal

6. What is the major product of the reaction shown above?

(A) H2O; H2SO4, heat; KMnO4; O3; Zn (B) LiAlH4; K2Cr2O7, H2O; NH2OH (C) LiAlH4; NaOH, heat; KMnO4 (D) H2O, H+; K2Cr2O7; NH2OH (E) LiAlH4; H2SO4, heat; O3; Zn 3. Which of the compounds below is the product of the following reaction? O C (CH2) 4CH3 H 2NNH 2

KOH heat

OH CH (CH 2)3CH 3

(A)

(CH2) 4CH3

(D) OH CH (CH 2)4CH 3

(B)

(CH2) 5CH3

(E) OCH 2 (CH 2)4CH 3

(C) 4. Which of the following reactions will produce a secondary amine?

7. The saponification of the optically active ester using isotopically labeled oxygen as shown above would most likely produce which of the following products?

11. Of the following, which reacts with methylamine (CH3NH2) to form the imine shown above? 8. Which of the following is a product of the reaction sequence shown above?

12. Which of the following correctly indicates the order of reactivity of the halides above with sodium iodide in acetone?

9. Which of the following structures is an intermediate formed in the amide hydrolysis shown above?

10. What is the major product of the reaction shown above?

13. Which of the following reactions would NOT be an acceptable method for the preparation of methyl benzoate?

14. Which of these reagents can accomplish the following reaction?

A. NaBH4 B. LiAlH4 C. NaH D. H3O+

15. Which of the following is an intermediate formed in the reaction below?

A.

C.

B.

D.

16-20: Determine the type of reaction: Choose : A. Nucleophilic Substitution B. Nucleophilic Addition C. Electrophilic Substitution D. Electrophilic Addition E. Free Radical Substitution F. Elimination G. Rearrangement 16. formation of hemiacetal 17. oxymercuration of styrene 18. conversion of allyl phenyl ether to o-allylphenol 19. reduction of acetaldehyde by NaBH4 20. acid hydrolysis of acetonitrile 21-25: Identify the type of reaction: Choices: A. Clemmensen reduction B. Wolf-Kishner reduction C. Aldol Condensation D. Cannizzaro reaction E. Claisen Condensation 21. C6H5CH2CHO + Zn(Hg), HCl  C6H5CH2CH3 22. HCHO + PhCHO + OH-  PhCH2OH + HCOO23. PhCOCH2CH3 + H2NNH2, OH-  PhCH2CH2CH3 24. 2 CH3CHO + KOH/H2O  CH3CH(OH)CH2CHO 25. CH3COOCH2CH3 + CH3CH2O-Na+  CH3COCH2COOCH2CH3